Hey, @ACWadmin1 !
Ok! I’m happy to report that stripping the EXIF data, rotating, and re-submitting has the correct image orientation for both the encounter image and for the one seen when matching in the iaResults.jsp page: Wildbook for Carnivores.
This feels very eerily similar to something Colin found on Seadragon the other day: SeadragonSearch annotation/match results issue - #6 by ChrissyTustison
He identified some software that is effective at rotating images in a way that won’t further confuse our poor ID algorithm, which I’ll reproduce here:
Stripping off the bad EXIF data: View Exif data online, remove Exif online
Rotate the raw image again and save: Rotate image online.
So, any time y’all end up needing to rotate an image for whatever reason, that would be the software I’d recommend to use for it.
Does this mystery of “skew” feel solved to you? 
-Mark